Tenika Gaither, who has nine children, was brought food and gifts by the men.
"God bless you all. God bless you all. I will never forget this," she told them.
Gaither is trying to rebuild her life after getting a divorce and Christmas was going to be put on hold this year - until "I am a Gentleman" showed up.
"I didn't really have enough for my children. This year we didn't really have anything," she said.
"I am so happy. I have never seen anything like this in my life," said daughter Tyteana Givens. "I am so grateful for what ya'll did for my brothers and my sister and my mom because she's really been going through hard times and to see her happy now. I am just as happy as she is."
"I am a Gentleman" surprised 10 families on Christmas Eve, traveling in a motorcade and escorted by Chicago police.
"As an organization, we are committed with the young men to take our personal time on Christmas Eve just to locate families throughout the Chicagoland area who have fallen on hard times just to show up and we show a major way," said Jermaine Anderson, of I Am A Gentleman, Inc.
For one family the group brought food, gifts and furniture. This is the fourth year they've done this program.
And the reaction by families never gets old.
Grandmother Diane Williams was speechless after they walked into her apartment spreading holiday cheer.
"I am excited and I am grateful because God remembered us," Williams said. "I have been one to always give back and it was so hard this year not to be able to do the things that I wanted to do. I didn't know how god was going to do it."